Methyl caffeate

Methyl caffeate
Names
Chemical structure of methyl caffeate
IUPAC name methyl (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
Other names Caffeic acid methyl ester methylcaffeate Methyl 3,4-dihydroxycinnamate
Identifiers
CAS Number	3843-74-1
ChemSpider	600455
Jmol interactive 3D	Image
PubChem	689075
InChI InChI=1S/C10H10O4/c1-14-10(13)5-3-7-2-4-8(11)9(12)6-7/h2-6,11-12H,1H3/b5-3+ Key: OCNYGKNIVPVPPX-HWKANZROSA-N InChI=1/C10H10O4/c1-14-10(13)5-3-7-2-4-8(11)9(12)6-7/h2-6,11-12H,1H3/b5-3+ Key: OCNYGKNIVPVPPX-HWKANZROBE
SMILES COC(=O)/C=C/C1=CC(=C(C=C1)O)O
Properties
Chemical formula	C₁₀H₁₀O₄
Molar mass	194.18 g/mol
Related compounds
Related compounds	Caffeic acid, Ethyl caffeate
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Methyl caffeate is an ester of an hydroxycinnamic acid, a naturally occurring phenolic compound.

Natural occurrences

It can be found in Polygonum amplexicaule var. sinense (Chinese name: Xuesanqi), a widely distributed medicinal plant in China^[1] and in the fruit of Solanum torvum.^[2]

Health effect

Methyl caffeate shows an antidiabetic effect in streptozotocin induced diabetic rats.^[2]

References

↑ Isolation, identification and determination of methyl caffeate, ethyl caffeate and other phenolic compounds from Polygonum amplexicaule var. sinense. Meixian Xiang, Hanwen Su, Jinyue Hu and Yunjun Yan, Journal of Medicinal Plants Research Vol., 4 May 2011, 5(9), pages 1685–1691 (abstract)
1 2 Antihyperglycemic activity and antidiabetic effect of methylcaffeate isolated from Solanum torvum Swartz. fruit in streptozotocin induced diabetic rats. Gopalsamy Rajiv Gandhi, Savarimuthu Ignacimuthu, Michael Gabriel Paulraj, Ponnusamy Sasikumar, European Journal of Pharmacology, Volume 670, Issues 2–3, 30 November 2011, Pages 623–631, doi:10.1016/j.ejphar.2011.09.159

External links

Types of hydroxycinnamic acids

Aglycones

Precursor	Cinnamic acid

Monohydroxycinnamic acids (Coumaric acids)	p-Coumaric acid o-Coumaric acid m-Coumaric acid

Dihydroxycinnamic acids	Caffeic acid (3,4-dihydroxycinnamic acid) Umbellic acid (2,4-dihydroxycinnamic acid) 2,3-Dihydroxycinnamic acid 2,5-Dihydroxycinnamic acid 3,5-Dihydroxycinnamic acid

Trihydroxycinnamic acids	3,4,5-Trihydroxycinnamic acid 3,4,6-Trihydroxycinnamic acid

O-methylated forms	Ferulic acid 5-Hydroxyferulic acid Sinapinic acid

others	Plicatin A Plicatin B

Esters

glycoside-likes

Esters of
caffeic acid
with cyclitols

esters of quinic acid	Chlorogenic acid (3-caffeoylquinic acid) Cryptochlorogenic acid (4-O-caffeoylquinic acid) Neochlorogenic acid (5-O-Caffeoylquinic acid) Cynarine (1,5-dicaffeoylquinic acid) 3,4-dicaffeoylquinic acid 3,5-dicaffeoylquinic acid

esters of shikimic acid	Dactylifric acid (3-O-caffeoylshikimic acid)

Glycosides

Ferulic acid glucoside
p-Coumaric acid glucoside
1-Sinapoyl-D-glucose

Tartaric acid esters

Caftaric acid
Cichoric acid (dicaffeoyltartaric acid)
Coutaric acid
Fertaric acid
Grape reaction product (caftaric acid conjugated with glutathione)

Other esters
with caffeic acid

Caffeoylmalic acid
Ethyl caffeate
Methyl caffeate
Caffeic acid phenethyl ester (CAPE)
Rosmarinic acid (ester with 3,4-dihydroxyphenyllactic acid)

Caffeoyl phenylethanoid
glycoside (CPG)

Echinacoside
Calceolarioside A, B, C and F
Chiritoside A, B and C
Cistanoside A, B, C, D, E, F, G an H
Conandroside
Myconoside
Pauoifloside
Plantainoside A
Plantamajoside
Tubuloside B
Verbascoside (Isoverbascoside, 2'-Acetylverbascoside)

Oligomeric forms

Dimers	Diferulic acids (DiFA) : 5,5'-Diferulic acid, 8-O-4'-Diferulic acid, 8,5'-Diferulic acid, 8,5'-DiFA (DC), 8,5'-DiFA (BF), 8,8'-Diferulic acid

Trimers	Triferulic acids : 5-5',8'-O-4"-Triferulic acid

Tetramers	Tetraferulic acids

Conjugates with
coenzyme A (CoA)

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